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Stereoselective Synthesis of Tetrahydropyran D ‐Ring of Methyl Sartortuoate
Author(s) -
Yao Hequan,
Gao Yuan,
Liu Peng,
Xu Xingxiang
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200990340
Subject(s) - tetrahydropyran , chemistry , geraniol , stereocenter , sharpless asymmetric dihydroxylation , kinetic resolution , stereoselectivity , stereochemistry , ring (chemistry) , yield (engineering) , dihydroxylation , enantioselective synthesis , organic chemistry , catalysis , materials science , chromatography , essential oil , metallurgy
A stereoselective synthesis of functionalized tetrahydropyran D ‐ring of methyl sartortuoate ( 1 ) was achieved starting from geraniol in a high yield. Sharpless asymmetric kinetic resolution, asymmetric dihydroxylation as well as asymmetric epoxidation were applied as key steps to establish all the four stereocenters of the D ‐ring.